4-Chloro-2-methylthiopyrimidine → 1-(2-Methylsulfanyl-pyrimidin-4-yl)-8-phenyl-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-6-one

HRID 1785464

Reaction equation

HRID 1785464 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]3[NH:14][CH2:13][CH2:12][CH2:11][N:10]3[C:15](=[O:17])[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.Cl[C:71]1[CH:76]=[CH:75][N:74]=[C:73]([S:77][CH3:78])[N:72]=1>C1(C)C=CC=CC=1>[CH3:78][S:77][C:73]1[N:74]=[C:75]([N:14]2[CH2:13][CH2:12][CH2:11][N:10]3[C:15](=[O:17])[CH:16]=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH:8]=[C:9]23)[CH:76]=[CH:71][N:72]=1

Participants

6

Reactant 4

HCID 971134-Chloro-2-methylthiopyrimidineHCID 634876Binap, (A+-)-HCID 125016018-Phenyl-1,2,3,4-tetrahydropyrido[1,2-a]pyrimidin-6-oneHCID 23676156Sodium t-butoxide

Product 1

HCID 575931211-(2-Methylsulfanyl-pyrimidin-4-yl)-8-phenyl-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-6-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 8-phenyl-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-6-one (1.86 g, 8.23 mmol), sodium tert-butoxide (1.6 g, 16 mmol), BINAP (0.15 g, 0.207 mmol), and Pd (OAc)2 (55 mg, 0.2 mmol) was added toluene (20 mL) and 4-chloro -2-methylthiopyrimidine (1.5 mL, 12 mmol). After purged with N2 for 10 min, the overall mixture was heated at 70° C. for 3 h prior to being cooled to room temperature. The resulting material was diluted with saturated NHCl(aq), water, and DCM. The organic layer was taken and the aqueous layer was extracted with DCM. The combined organic layers were dried over Na2SO4, filtrated, and concentrated. Column chromatographic purification (3% MeOH in DCM) of the crude residue afforded the title compound as a yellow solid. MS m/e 351 (M+H)+.

Workup

  1. customAfter purged with N2 for 10 min
  2. temperatureto being cooled to room temperature
  3. additionThe resulting material was diluted with saturated NHCl(aq), water, and DCM
  4. extractionthe aqueous layer was extracted with DCM
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltrated
  7. concentrationconcentrated
  8. customColumn chromatographic purification (3% MeOH in DCM) of the crude residue

Sources & evidence

ORD record
ord-4adc0ba0538a4090bb0ebdd5cc78d520
Source dataset
uspto-grants-2009_03
Patent number
US07504403B2

Linked notes

Loading…